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http://dx.doi.org/10.5012/jkcs.2012.56.5.603

Synthesis of Perfluoroalkyl Alcohol, 3-(Perfluorooctyl)propan-2-ol, Using Two-Step Alcoholization  

Nguyen, Trung Hieu (Department of Chemical Engineering, Hankyong National University)
Tae, Beom-Seok (Department of Chemical Engineering, Hankyong National University)
Park, Jun-Seo (Department of Chemical Engineering, Hankyong National University)
Lee, Kwang-Nam (Department of Chemical Engineering, Hankyong National University)
Publication Information
Journal of the Korean Chemical Society / v.56, no.5, 2012 , pp. 603-608 More about this Journal
Abstract
3-(Perfluorooctyl)propan-2-ol was synthesized using an alcoholization process. The synthesis consisted of two steps: (1) addition of the olefin propylene to perfluorooctyl iodide to yield the corresponding iodo-adduct perfluorooctyl propyl iodide and (2) hydrolysis of the adduct reacted with water and dimethylformamide to yield the final product. The adduct and product were analyzed using gas chromatography to determine the yield and purity. The optimal conditions for each step of the process were determined, and a 93% yield of adduct and 95% yield of final product was achieved.
Keywords
Perfluoroalkyl alcohol; Perfluoroalkyl iodide; Alcoholization; Fluorinated surfactant;
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1 Stuart, B.; Prichard, E. In Practical Laboratory Skills Training Guides; LGC, Teddington, UK: Cambridge, 2003; p 1.
2 Grob, R. L.; Barry, E. F. In Modern Practice of Gas Chromatography; John Wiley & Sons, Inc.: New Jersey, 2004; p 25.
3 Fromel, T.; Knepper, T. P. In Reviews of Environmental Contamination and Toxicology: Perfluorinated Alkylated Substances; Whitacre, D. M.; Voogt, P. d., Ed.; Springer: New York, 2010; Vol. 208, p 161.
4 Brace, N. O. J. Fluorine Chem. 1999, 93, 1.   DOI
5 Petrov, V. A.; Krespan, C. G. J. Fluorine Chem. 2000, 102, 199.   DOI
6 Lewandowski, G.; Meissner, E.; Milchert, E. J. Fluorine Chem. 2006, 127, 337.   DOI
7 Davis, C. R.; Burton, D. J.; Yang, Z.-Y. J. Fluorine Chem. 1995, 70, 135.   DOI
8 Hayashi, T.; Matsuo, M. U.S. Patent 4001309 (to Asahi Glass Company, Ltd., Tokyo, Japan), 1977.
9 Brace, N. O. J. Fluorine Chem. 2005, 126, 7.   DOI
10 Brace, N. O. J. Fluorine Chem. 1999, 96, 101.   DOI
11 Brace, N. O. J. Fluorine Chem. 2001, 108, 147.   DOI
12 Gambaretto, G.; Conte, L.; Fornasieri, G.; Zarantonello, C.; Tonei, D.; Sassi, A.; Bertani, R. J. Fluorine Chem. 2003, 121, 57.   DOI
13 Paterová, J.; Skalický, M.; Rybácková, M.; Kvícalová, M.; Cvacka, J.; Kvícala, J. J. Fluorine Chem. 2010, 131, 1338.   DOI
14 Yoneda, N. J. Fluorine Chem. 2004, 125, 7.   DOI
15 Bargigia, G.; Tonelli, C.; Tortelli, V. U.S. Patent 4748282 (to Ausimont S.p.A., Milan, Italy), 1988
16 Day, R. I. U.S. Patent 3283012 (to E.I. Du Pont de Nemours), 1966.
17 Loganathan, B. G.; Sajwan, K. S.; Sinclair, E.; Senthil Kumar, K.; Kannan, K. Water Res. 2007, 41, 4611.   DOI   ScienceOn
18 McNair, H. M.; Miller, J. M. In Basic Gas Chromatography; John Wiley & Sons, Inc.: New York, 1997; p 1.
19 Kissa, E. In Fluorinated Surfactants and Repellents; Marcel Dekker, Inc.: New York, 2001; Vol. 97, p 1.
20 Lehmler, H. J. Chemosphere 2005, 58, 1471.   DOI